If you have a Chuck rotary, it is 1 rotation of the chuck. If you have a Roller rotary, it is one rotation of the roller. You put the cup on too soon. Check with the Test button again, but without the cup.
From what I read it looks like you are very close to being done.
Rotary - Roller and Chuck confusion.
mm/rev is for setting the rotary so it makes EXACTLY one revolution and back when the Test button is pressed. This helps calibrate the rotary.
Chuck - Circumference is for telling Lightburn to increase or decrease the amount of travel on the surface of the item under the laser.
Roller - Circumference of the part does not matter. Lightburn uses the surface of the roller, which is 1:1 link to the part, to manage how far the surface of the part under the laser moves.
When working with a Rotary, imagine you are drawing on a flat surface, then wrapping that surface around your part. To make the resultant design look better on a curved or tapered surface, there are special Tools for finalizing your design.
I realize this may appear self-promoting, but check out this posting…
And here is one by one of our Guru Guys ( @misken ) :